1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(4-(5-iodo-2-methoxypyrimidin-4-yloxy)phenyl)-5-methylpyridin-2-amine

Participants

Reaction Steps

To a stirred mixture of 5-iodo-2-methoxypyrimidin-4(1H)-one (0.12 g, 0.46 mmol) and (1H-benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate(V) (0.24 g, 0.55 mmol) in acetonitrile (4 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.14 mL, 0.91 mmol). The reaction mixture was stirred at room temperature for 30 min before 4-(5-methylpyridin-2-ylamino)phenol (0.27 g, 1.37 mmol) was added. The reaction mixture was stirred at room temperature for an additional 1 h. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was separated, washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography to give N-(4-(5-iodo-2-methoxypyrimidin-4-yloxy)phenyl)-5-methylpyridin-2-amine. MS (ESI, pos. ion) m/z: 435.1 (M+1).

Provenance & Evidence